Acetic Acid → Methyl 3-hydroxy-5-methoxy-1-phenyl-1H-indole-2-carboxylate

HRID 1982416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1982416
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[N:12]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C[O-].[Na+].C(O)(=O)C>CO>[CH3:23][O:22][C:20]([C:19]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]2[C:4]([C:3]=1[OH:2])=[CH:9][C:8]([O:10][CH3:11])=[CH:7][CH:6]=2)=[O:21]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 13220377HCID 13220377, Verbindung

Produkt 1

HCID 54696100Methyl 3-hydroxy-5-methoxy-1-phenyl-1H-indole-2-carboxylateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A mixture of 1.7 kg (5.2 mole) of 5-methoxy-2-[(2-methoxy-2-oxoethyl)phenylamino]benzoic acid methyl ester, and 303 g (5.6 mole) of sodium methoxide in 10.0 l of anhydrous methanol was stirred at reflux for 90 minutes. The mixture was cooled to 20° C., filtered, and treated with 336 g (320 ml, 5.6 mole) of glacial acetic acid. The mixture was cooled in ice, and the precipitated crude product was filtered and washed with cold methanol followed by hexane. There was obtained 1267 g (82% yield) of the indole product of analytical purity, mp 114°-116° C.

Aufarbeitung

  1. temperatureat reflux for 90 minutes
  2. filtrationfiltered
  3. temperatureThe mixture was cooled in ice
  4. customthe precipitated crude product
  5. filtrationwas filtered
  6. washwashed with cold methanol

Quellen und Nachweise

ORD-Eintrag
ord-7da37bf95621464dbb8f079410dddfe1
Quelldatensatz
uspto-grants-1986_06
Patentnummer
US04596814

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